N‑Acyl Dehydrotyrosines, Tyrosinase Inhibitors from the Marine Bacterium Thalassotalea sp. PP2-459

• Published in: Journal of natural products (Washington, D.C.) Vol. 79; no. 2; pp. 447 - 450
• Main Authors: Deering, Robert W, Chen, Jianwei, Sun, Jiadong, Ma, Hang, Dubert, Javier, Barja, Juan L, Seeram, Navindra P, Wang, Hong, Rowley, David C
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 26.02.2016; Amer Chemical Soc
• Subjects: Arbutin - pharmacology; Chemistry, Medicinal; Gram-Negative Bacteria - chemistry; Life Sciences & Biomedicine; Marine Biology; Molecular Structure; Monophenol Monooxygenase - antagonists & inhibitors; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Sciences; Proteobacteria - chemistry; Pyrones - pharmacology; Science & Technology; Spain; Tyrosine - analogs & derivatives; Tyrosine - chemistry; Tyrosine - isolation & purification; Tyrosine - pharmacology; Spain; RECLASSIFICATION; ENVIRONMENTAL DNA; PRODUCTS; BIOSYNTHESIS; THALASSOMONAS; GENUS THALASSOTALEA; SP NOV; EMENDED DESCRIPTION; COMB. NOV
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.5b00972

Thalassotalic acids A–C and thalassotalamides A and B are new N-acyl dehydrotyrosine derivatives produced by Thalassotalea sp. PP2-459, a Gram-negative bacterium isolated from a marine bivalve aquaculture facility. The structures were elucidated via a combination of spectroscopic analyses emphasizing two-dimensional NMR and high-resolution mass spectrometric data. Thalassotalic acid A (1) displays in vitro inhibition of the enzyme tyrosinase with an IC50 value (130 μM) that compares favorably to the commercially used control compounds kojic acid (46 μM) and arbutin (100 μM). These are the first natural products reported from a bacterium belonging to the genus Thalassotalea.